P
US4767779AExpiredUtilityPatentIndex 69

Pyrazoline-1-carboxamides, composition containing them, and insecticidal method of using them

Assignee: FMC CORPPriority: Sep 24, 1985Filed: Apr 9, 1986Granted: Aug 30, 1988
Est. expirySep 24, 2005(expired)· nominal 20-yr term from priority
Inventors:DUGGAN ANGELINA J
C07D 405/12A01N 47/38C07D 405/14C07D 405/04C07D 231/06
69
PatentIndex Score
9
Cited by
8
References
33
Claims

Abstract

Pyrazolines of the following formula are insecticides: ##STR1## wherein R A , R B and R C are aromatic groups; R N is hydrogen or lower alkyl; and W is oxygen or sulfur.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. An insecticidal pyrazoline of the formula ##STR11## wherein R A  is of the formula ##STR12##  in which R' A  is selected from hydrogen, halogen, lower alkyl, lower alkoxy, lower haloalkoxy, lower alkynyloxy and lower haloalkyl; or R A  is of the formula ##STR13##  in which X is a bridge of the formula   --O--(CR'.sub.AA R'.sub.AB).sub.a --O.sub.a'      wherein a is 1-3, a' is 0 or 1, a+a' is at least 2 but no greater than 3, R' AA  and R' AB  are independently selected from hydrogen, halogen and lower alkyl, and R' AC  is selected from hydrogen, halogen, lower alkyl, lower alkoxy, lower haloalkoxy, and lower haloalkyl;   R B  is a 4- or 5-substituent of the formula ##STR14##  in which R' B  is selected from hydrogen, halogen, lower alkyl, lower alkoxy, and lower haloalkyl; or R B  is of the formula ##STR15##  in which Y is a bridge of the formula   --O--(CR'.sub.BA R'.sub.BB).sub.b --O.sub.b'        wherein b is 1-3, b' is 0 or 1, b+b' is at least 2 but no greater than 3, R' BA  and R' BB  are independently selected from hydrogen, halogen and lower alkyl, and R' BC  is selected from hydrogen, halogen, lower alkyl, lower alkoxy, lower haloalkoxy, and lower haloalkyl;   R C  is of the formula ##STR16##  in which R D  is selected from hydrogen and lower alkyl; R E  is selected from halogen, alkoxy, containing 1-4 carbon atoms, lower haloalkoxy, lower haloalkyl, cyano, nitro, phenyl, phenoxy, benzoyl, benzoyloxy, --NR F  R G  wherein R F  and R G  are independently lower alkyl, and --SO n  R H  wherein R H  is lower alkyl and n is 0-2; or R C  is of the formula ##STR17##  in which Z is a bridge of the formula   --O--(CR'.sub.CA R'.sub.CB).sub.c --O.sub.c' --        wherein c is 1-3, c' is 0 or 1, c+c' is at least 2 but no greater than 3, R' CA  and R' CB  are independently selected from hydrogen, halogen and lower alkyl, with the proviso that R' CA  and R' CB  are not both hydrogen when c is 1 and c' is 1, and R' CC  is selected from hydrogen, halogen, lower alkyl, lower alkoxy, lower haloalkoxy, and lower haloalkyl; provided that when R A  is a compound of group I and R B  is a compound of group III, R C  is not a compound of group V;   R N  is hydrogen or lower alkyl; and   V and W are independently oxygen or sulfur.   
     
     
       2. A compound of claim 1 wherein W is oxygen. 
     
     
       3. A compound of claim 1 wherein R' A  is halogen or lower haloalkoxy. 
     
     
       4. A compound of claim 1 wherein R B  is a 4-substituent. 
     
     
       5. A compound of claim 1 wherein R B  is of the formula ##STR18## 
     
     
       6. A compound of claim 5 wherein R' B  is halogen. 
     
     
       7. A compound of claim 1 wherein R C  is of the formula ##STR19## or is selected from 2,3-dihydro-2,2-dimethylbenzofuran-5-yl, 2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl, 2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-6-yl, 2,2-difluoro-1,3-benzodioxol-5-yl, and 2,2-dimethyl-1,3-benzodioxol-5-yl. 
     
     
       8. A compound of claim 1 wherein R C  is of the formula ##STR20## 
     
     
       9. A compound of claim 8 wherein R E  is lower haloalkoxy. 
     
     
       10. 3-(4-Difluoromethoxyphenyl)-N-(2,3-dihydro-2,2-dimethylbenzofuran-5-yl)-4-phenylpyrazoline-1-carboxamide, a compound of claim 1. 
     
     
       11. 3,4-bis(4-Fluorophenyl)-N-(2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl)pyrazoline-1-carboxamide, a compound of claim 1. 
     
     
       12. 3,4-bis(4-Fluorophenyl)-N-(2,3-dihydro-2,2-dimethylbenzofuran-5-yl)pyrazoline-1-carboxamide, a compound of claim 1. 
     
     
       13. N-(2,3-Dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl)-3-(4-difluoromethoxyphenyl -4-phenylpyrazoline-1-carboxamide, a compound of claim 1. 
     
     
       14. N-(2,2-Difluoro-1,3-benzodioxol-5-yl)-3-(4-difluoromethoxyphenyl)-N-methyl-4-phenylpyrazoline-1-carboxamide, a compound of claim 1. 
     
     
       15. 3,4-bis(4-Chlorophenyl)-N-(2,2-dimethyl-1,3-benzodioxol-5-yl)pyrazoline-1-carboxamide, a compound of claim 1. 
     
     
       16. N-(2,2-Difluoro-1,3-benzodioxol-5-yl)-3,4-bis-(4-fluorophenyl)pyrazoline-1-carboxamide, a compound of claim 1. 
     
     
       17. 3-(4-Chlorophenyl)-N-(2,2-difluoro-1,3-benzodioxol-5-yl)-4-(4-fluorophenyl)pyrazoline-1-carboxamide, a compound of claim 1. 
     
     
       18. 3-(4-Difluoromethoxyphenyl)-N-(2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl)-N-methyl-4-phenylpyrazoline-1-carboxamide, a compound of claim 1. 
     
     
       19. 3-(4-Difluoromethoxyphenyl)-4-(4-fluorophenyl) -N-(2,3-dihydro-2,2,3,3,-tetrafluorobenzofuran-5-yl)pyrazoline-1-carboxamide, a compound of claim 1. 
     
     
       20. 3-(4-Difluoromethoxyphenyl)-4-(4-fluorophenyl)-N-(2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-6-yl)pyrazoline-1-carboxamide, a compound of claim 1. 
     
     
       21. 4-(4-Chlorophenyl)-N-(2,3-dihydro-2,2-dimethylbenzofuran-5-yl)-3-phenylpyrazoline-1-carboxamide, a compound of claim 1. 
     
     
       22. 3-(4-Chlorophenyl)-4-(4-fluorophenyl)-N-(2,3-dihydro-2,2-dimethylbenzofuran-5-yl)pyrazoline-1-carboxamide, a compound of claim 1. 
     
     
       23. 3-(4-Difluoromethoxyphenyl)-4-(4-fluorophenyl)-N-(2,3-dihydro-2,2-dimethylbenzofuran-5-yl)pyrazoline-1-carboxamide, a compound of claim 1. 
     
     
       24. 4-(4-Chlorophenyl)-3-(4-difluoromethoxyphenyl)-N-(2,3-dihydro-2,2-dimethylbenzofuran-5-yl)pyrazoline-1-carboxamide, a compound of claim 1. 
     
     
       25. 3,4-bis(4-Chlorophenyl)-N-(2,2-difluoro-1,3-benzodioxol-5-yl)pyrazoline-1-carboxamide, a compound of claim 1. 
     
     
       26. 3,4-bis(4-Chlorophenyl)-N-(2,3-dihydro-2,2-dimethylbenzofuran-5-yl)pyrazoline-1-carboxamide, a compound of claim 1. 
     
     
       27. 3-(4-Chlorophenyl)-N-(2,3-dihydro-2,2-dimethylbenzofuran-5-yl)-4-phenylpyrazoline-1-carboxamide, a compound of claim 1. 
     
     
       28. 3-(4-Chlorophenyl)-4-phenyl-N-[4-(4-trifluoromethylphenoxy)phenyl]pyrazonline-1-carboxamide. 
     
     
       29. An insecticidal composition comprising an insecticidally effective amount of a compound of claim 1 in admixture with a compatible, agriculturally acceptable carrier, diluent, adjuvant, or complementary pesticide. 
     
     
       30. A composition of claim 29 wherein W is oxygen. 
     
     
       31. A composition of claim 29 wherein R' A  is halogen or lower haloalkoxy. 
     
     
       32. A composition of claim 29 wherein R B  is a 4-substituent. 
     
     
       33. A method for controlling insects which comprises applying to the locus where control is desired an insecticidally effective amount of a compound of claim 1.

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